<p>Oxidative synthesis of pyrazoles from aromatic alcohols and phenyl hydrazine has been achieved by using trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate and KOH. The reaction proceeds via oxidative coupling of primary and secondary alcohols with phenylhydrazines by singlet molecular oxygen produced from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate at room temperature, and broad range of derivatives were obtained in good to excellent yields. Advantageous features of the present methodology include mild reaction conditions, transition metal-free, good functional-group tolerance, use of readily available primary and secondary alcohols and so on.</p> Graphical abstract <p>Oxidative synthesis of pyrazoles from aromatic alcohols and phenyl hydrazine has been achieved by using trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate/KOH. The reaction proceeds via oxidative coupling of primary and secondary alcohols with phenylhydrazines by singlet oxygen produced from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate and a range of derivatives were obtained in good to excellent yields</p>

错误:搜索内容不能为空,请输入英文关键词
错误:关键词超出字数限制,请精简
高级检索

Monoacetylated bishydroperoxide-derived singlet molecular oxygen-mediated oxidative coupling of primary and secondary alcohols with phenylhydrazine: Synthesis of 1,3,5-trisubstituted pyrazoles

  • Z Najminejad,
  • D Azarifar,
  • S-M Khatami

摘要

Oxidative synthesis of pyrazoles from aromatic alcohols and phenyl hydrazine has been achieved by using trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate and KOH. The reaction proceeds via oxidative coupling of primary and secondary alcohols with phenylhydrazines by singlet molecular oxygen produced from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate at room temperature, and broad range of derivatives were obtained in good to excellent yields. Advantageous features of the present methodology include mild reaction conditions, transition metal-free, good functional-group tolerance, use of readily available primary and secondary alcohols and so on.

Graphical abstract

Oxidative synthesis of pyrazoles from aromatic alcohols and phenyl hydrazine has been achieved by using trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolan-3-yl ethaneperoxate/KOH. The reaction proceeds via oxidative coupling of primary and secondary alcohols with phenylhydrazines by singlet oxygen produced from trans-5-hydroperoxy-3,5-dimethyl-1,2-dioxolane-3-yl ethaneperoxate and a range of derivatives were obtained in good to excellent yields